Patent GB-283510-A (GB)
Abstract: 283,510. I. G. Farbenindustrie Akt.- Ges. Jan. 11, 1927, [Convention date]. Samples furnished. Nitro-9-aminoacridine derivatives which contain either in the 9-amino group or in the nucleus a tertiary nitrogen atom are prepared either by condensing a nitro-9-chloracridine with a base containing at least two basic nitrogen atoms, including both a primary one and a tertiary one of strongly basic character, or by condensing a nitro-9-chloracridine containing a tertiary nitrogen atom of strongly basic character in one or more groups which are substituents in the nucleus with ammonia or a primary or secondary amine. The 9-chloraoridine may be replaced by the corresponding 9-ethers. The products have a strong bactericidal action. According to examples there are obtained, (1) 7-ethoxy-3-nitro-9-(#- diethylaminoethylamino)-acridine by heating 7- ethoxy-3-nitro-9-chloracridine with phenol and condensing the resulting 9-phenylether, without isolation, with as-diethylethylenediamine; (2) 7 ethoxy -3-nitro-9-(gamma-diethylamino-#-hydroxypropylamino)-acridine from the ethoxynitrochloracridine and gamma-diethylamino-#-hydroxypropylamine (Specification 275,622); (3) 7-ethoxy-3-nitro-9-(p- #-diethylaminoethylamino-phenylamino) - acridine from the ethoxynitrochloracridine and N-diethyl- N<1>-(p-aminophenyl)-ethylenediamine; (4) 7- ethoxy-3-nitro-9-(p-gamma-diethylamino-#- hydroxypropylamino-phenylamino)-acridine, from the ethoxynitrochloracridine and 1-diethylamino-2-hydroxy- 3-(p-aminophenylamino)-propane; (5) 7-ethoxy-3- nitro-9-(p-gamma-#<1>-diethylaminoethylamino-#-hydroxypropylamino-phenylamino)-acridine from the ethoxynitrochloracridine and 1-#-diethylaminoethylamino-2-hydroxy-3-paminophenylaminopropane; (6) 7-ethoxy-3 : 6-dinitro-9-(p-#-diethylaminoethoxyphenylamino)-acridine from 7-ethoxy-3:6-dinitro-9-chloracridine and p-aminophenol-#-diethylaminoethyl ether; (7) 7-#-diethylaminoethoxy-3-nitro-9-aminoacridine by treating 7-#-diethylamincethoxy-3-nitro-9-chloracridine in phenol solution with ammonia. Specification 176,038 is referred to. N-Diethyl-N<1>-p-aminophenyl-ethylenediamine is obtained by condensing chlorethyldiethylamine with p-nitraniline or p-aminoacetanilide and reducing or saponifying. 1-Diethylamino- or 1-diethylaminoethylamino- 2-hydroxy-3-p-aminophenylaminopropane is obtained by condensing p-aminoacetanilide with epichlorhydrin, exchanging the chlorine for the diethylamine or the' as-diethylethylenediamine residue, and splitting off the acetyl group. 9-Chloracridine derivatives.-7-Ethoxy-3 : 6-dinitro-9-chloracridine is obtained by condensing 2- nitro-4-aminophenetole with 2-chlor-4-nitrobenzoic acid in presence of amyl alcohol, potassium carbonate, and copper, converting the 5 : 5<1>-dinitro-4<1>-ethoxydiphenylamine-2-carboxylic acid into 7-ethoxy-3 : 6-dinitroacridone (by Ullmann's method, namely by means of phosphorus pentachloride and then alminium chloride) and treating the acridone with phosphorus pentachloride 7-#-diethylamino-ethoxy-3-nitro-9-chloraoridine is similarly obtained from 2-chlor-4-nitrobenzoic acid and p-aminophenol-#-diethylaminoethyl ether by way of the 4<1>-#-diethylaminoethoxy-5- nitrodiphenylamine-2-carboxylic acid and the 2- #-diethylaminoethoxy-6-nitroacridone p-Aminophenol-#-diethylaminoethylether is obtained from sodium p-acetaminophenolate and #- diethylaminoethylchloride and removal of acetyl group from the product.